Methyl 5-bromopyridine-3-carboxylate → Methyl 5-(4-ethylphenyl)pyridine-3-carboxylate

HRID 876220Notes

Reaction equation

HRID 876220 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:12]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)[CH3:13]>>[CH2:12]([C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[N:4][CH:3]=2)=[CH:16][CH:15]=1)[CH3:13]

Participants

3

Reactant 2

HCID 699336Methyl 5-bromopyridine-3-carboxylateHCID 2734352Boronic acid, (4-ethylphenyl)-

Product 1

HCID 58002322Methyl 5-(4-ethylphenyl)pyridine-3-carboxylate

Procedure

32 g (148 mmol) of methyl 5-bromonicotinate and 27 g (178 mmol, 1.2 eq.) of 4-ethylphenylboronic acid were reacted according to General Method 1A. Yield: 24 g (64% of theory)

Sources & evidence

ORD record
ord-5873b30830314ccc95f868efa4c8f22a
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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